Hydrazine → 5-Fluoro-3-Phenyl-1H-Indazole

HRID 1349583Notes

Reaction equation

HRID 1349583 reaction equation
F[C:2]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[NH2:17][NH2:18]>N1C=CC=CC=1>[F:16][C:13]1[CH:12]=[C:3]2[C:2](=[CH:15][CH:14]=1)[NH:18][N:17]=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 5228262,5-Difluorobenzophenone

Product 1

HCID 131437095-Fluoro-3-Phenyl-1H-IndazoleYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2,5-difluorobenzophenone (0.655 g, 3.0 mmol) and hydrazine (1.0 mL) in dried pyridine (10 mL) was heated at 130° C. for 5 hours and then concentrated and purified by chromatography (SiO2, 15–30% ethyl acetate/hexane) to provide the title compound (0.254 g, 40% yield): mp 124–125° C.; 1H NMR (CDCl3) δ 10.89 (br s, 1H), 7.94 (d, 2H), 7.65 (dd, 1H), 7.42–7.54 (m, 3H), 7.33 (dd, 1H), 7.21 (dt, 1H); EI-MS (m/z) 212 [M]+.

Workup

  1. concentrationconcentrated
  2. custompurified by chromatography (SiO2, 15–30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5c5a9f52ec9d4940a39ba0abdb31a0cb
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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